Losartan potassium, valsartan, olmesartan medoxomil, candesartan cilexetil, telmisartan, irbesartan and the like are useful as angiotensin II receptor blockers.
As a production method of these compounds, for example, the production method described in J. Org. Chem., 1994, vol. 59, pages 6391-6394 (non-patent document 1) is known as a synthesis method of losartan, the production method described in Org. Process Res. Dev., 2007, vol. 11, pages 892-898 (non-patent document 2) is known as a synthesis method of valsartan, and the production method described in J. Med. Chem., 1993, vol. 36, pages 3371-3380 (non-patent document 3) is known as a synthesis method of irbesartan.
As a production method of olmesartan, the production methods described in JP-B-7-121918 (patent document 1), JP-A-2010-505926 (patent document 2), WO 2004/085428 (patent document 3) and the like are known.
Also, as a conventional method of biphenylation reaction, for example, the method described in Chem. Lett., 2008, vol. 37, NO. 9, pages 994-995 (non-patent document 4), and the methods described in Tetrahedron, 2008, vol. 64, pages 6051-6059 (non-patent document 5), Angewandte Chemie International Edition, 2009, vol. 48, pages 9792-9827 (non-patent document 6), and WO 2011/061996 (patent document 4) are known.